RU2007126745A - NEW HYDANTOIN DERIVATIVES AS METALLOPROTEINASIS INHIBITORS - Google Patents

NEW HYDANTOIN DERIVATIVES AS METALLOPROTEINASIS INHIBITORS Download PDF

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RU2007126745A
RU2007126745A RU2007126745/04A RU2007126745A RU2007126745A RU 2007126745 A RU2007126745 A RU 2007126745A RU 2007126745/04 A RU2007126745/04 A RU 2007126745/04A RU 2007126745 A RU2007126745 A RU 2007126745A RU 2007126745 A RU2007126745 A RU 2007126745A
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compound
pharmaceutically acceptable
acceptable salt
methyl
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Балинт ГАБОС (SE)
Балинт Габос
Микаэль ЛУНДКВИСТ (SE)
Микаэль Лундквист
АФ РОЗЕНШЕЛЬД Магнус МУНК (SE)
Аф Розеншельд Магнус Мунк
Игорь ШАМОВСКИ (SE)
Игорь ШАМОВСКИ
Павол ЗЛАТОЙДСКИ (SE)
Павол ЗЛАТОЙДСКИ
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Астразенека Аб (Se)
Астразенека Аб
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
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    • A61P11/00—Drugs for disorders of the respiratory system
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Pulmonology (AREA)
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  • Physical Education & Sports Medicine (AREA)
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  • Pain & Pain Management (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (15)

1. Соединение формулы (I) или его фармацевтически приемлемая соль1. The compound of formula (I) or its pharmaceutically acceptable salt
Figure 00000001
,
Figure 00000001
, где R1 представляет собой Н, галоген, CF3 или CH2CN;where R 1 represents H, halogen, CF 3 or CH 2 CN; R2 представляет собой C1-3алкил; иR 2 represents C 1-3 alkyl; and каждый из А, А1 и В независимо представляет собой СН или N.each of A, A 1 and B independently represents CH or N. 2. Соединение по п.1, где R1 представляет собой хлор.2. The compound according to claim 1, where R 1 represents chlorine. 3. Соединение по п.1, где R1 представляет собой CF3.3. The compound according to claim 1, where R 1 represents CF 3 . 4. Соединение по п.1, где R2 представляет собой метил или этил.4. The compound according to claim 1, where R 2 represents methyl or ethyl. 5. Соединение по п.1, где каждый из А и А1 представляет собой N.5. The compound according to claim 1, where each of A and A 1 represents N. 6. Соединение по п.1, выбранное из группы, состоящей из6. The compound according to claim 1, selected from the group consisting of (5S)-5-метил-5-({[6-[2-(трифторметил)пиримидин-5-ил]-3,4-дигидроизохинолин-2(1Н)-ил]сульфонил}метил)имидазолидин-2,4-диона;(5S) -5-methyl-5 - ({[6- [2- (trifluoromethyl) pyrimidin-5-yl] -3,4-dihydroisoquinolin-2 (1H) -yl] sulfonyl} methyl) imidazolidine-2,4 dione; (5S)-5-({[6-(4-хлорфенил)-3,4-дигидроизохинолин-2(1Н)-ил]сульфонил}метил)-5-метилимидазолидин-2,4-диона;(5S) -5 - ({[6- (4-chlorophenyl) -3,4-dihydroisoquinolin-2 (1H) -yl] sulfonyl} methyl) -5-methylimidazolidin-2,4-dione; {4-[2-({[(4S)-4-метил-2,5-диоксоимидазолидин-4-ил]метил}сульфонил)-1,2,3,4-тетрагидроизохинолин-6-ил]фенил}ацетонитрила;{4- [2 - ({[(4S) -4-methyl-2,5-dioxoimidazolidin-4-yl] methyl} sulfonyl) -1,2,3,4-tetrahydroisoquinolin-6-yl] phenyl} acetonitrile; (5S)-5-метил-5-{[(6-пиридин-3-ил-3,4-дигидроизохинолин-2(1H)-ил)сульфонил]метил}имидазолидин-2,4-диона;(5S) -5-methyl-5 - {[(6-pyridin-3-yl-3,4-dihydroisoquinolin-2 (1H) -yl) sulfonyl] methyl} imidazolidin-2,4-dione; (5S)-5-({[6-(4-хлорфенил)-3,4-дигидро-2,7-нафтиридин-2(1H)-ил]сульфонил}метил)-5-метилимидазолидин-2,4-диона;(5S) -5 - ({[6- (4-chlorophenyl) -3,4-dihydro-2,7-naphthyridin-2 (1H) -yl] sulfonyl} methyl) -5-methylimidazolidine-2,4-dione ; и его фармацевтически приемлемые соли.and its pharmaceutically acceptable salts. 7. Способ получения соединения формулы (I), как определено в п.1, или его фармацевтически приемлемой соли, включающий7. A method for producing a compound of formula (I) as defined in claim 1, or a pharmaceutically acceptable salt thereof, comprising а) взаимодействие соединения формулы (II)a) the interaction of the compounds of formula (II)
Figure 00000002
,
Figure 00000002
, где R2 такой, как определено в формуле (I), и L1 представляет собой уходящую группу, с соединением формулы (III) (или его солью)where R 2 is as defined in formula (I), and L 1 is a leaving group, with a compound of formula (III) (or a salt thereof)
Figure 00000003
,
Figure 00000003
, где R1, А, А1 и В такие, как определено в формуле (I); илиwhere R 1 , A, A 1 and B are as defined in formula (I); or б) взаимодействие соединения формулы (V)b) the interaction of the compounds of formula (V)
Figure 00000004
Figure 00000004
 где R2 и В такие, как определено в формуле (I), и LG представляет собой уходящую группу; с производным бороновой кислоты формулы (XII)where R 2 and B are as defined in formula (I), and LG is a leaving group; with a boronic acid derivative of the formula (XII)
Figure 00000005
,
Figure 00000005
, где R1, А и А1 такие, как определено в формуле (I); илиwhere R 1 , A and A 1 are as defined in formula (I); or в) взаимодействие соединения формулы (IX)C) the interaction of the compounds of formula (IX)
Figure 00000006
,
Figure 00000006
, где R1, R2, А, А1 и В такие, как определено в формуле (I);where R 1 , R 2 , A, A 1 and B are as defined in formula (I); с карбонатом аммония и цианидом калия;with ammonium carbonate and potassium cyanide; и возможно после этого получение его фармацевтически приемлемой соли.and thereafter, obtaining a pharmaceutically acceptable salt thereof is possible. 8. Фармацевтическая композиция, содержащая соединение формулы (I) или его фармацевтически приемлемую соль по любому из пп.1-6 вместе с фармацевтически приемлемым вспомогательным веществом, разбавителем или носителем.8. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6, together with a pharmaceutically acceptable excipient, diluent or carrier. 9. Способ получения фармацевтической композиции по п.8, включающий смешивание соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6 с фармацевтически приемлемым вспомогательным веществом, разбавителем или носителем.9. A method of obtaining a pharmaceutical composition according to claim 8, comprising mixing a compound of formula (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6 with a pharmaceutically acceptable excipient, diluent or carrier. 10. Соединение формулы (I) или его фармацевтически приемлемая соль по любому из пп.1-6 для применения в терапии.10. The compound of formula (I) or its pharmaceutically acceptable salt according to any one of claims 1 to 6 for use in therapy. 11. Применение соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6 в изготовлении лекарственного средства для применения в лечении обструктивного заболевания дыхательных путей.11. The use of a compound of formula (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6 in the manufacture of a medicament for use in the treatment of obstructive airway disease. 12. Применение по п.11, где обструктивное заболевание дыхательных путей представляет собой астму или хроническое обструктивное заболевание легких.12. The use of claim 11, wherein the obstructive airway disease is asthma or chronic obstructive pulmonary disease. 13. Применение соединения (I) или его фармацевтически приемлемой соли по любому из пп.1-6 в изготовлении лекарственного средства для применения в лечении ревматоидного артрита, остеоартрита, атеросклероза, рака или рассеянного склероза.13. The use of compound (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6 in the manufacture of a medicament for use in the treatment of rheumatoid arthritis, osteoarthritis, atherosclerosis, cancer or multiple sclerosis. 14. Способ лечения заболевания или состояния, опосредованного ММР12 и/или ММР9, включающий введение пациенту терапевтически эффективного количества соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6.14. A method of treating a disease or condition mediated by MMP12 and / or MMP9, comprising administering to a patient a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6. 15. Способ лечения обструктивного заболевания дыхательных путей, включающий введение пациенту терапевтически эффективного количества соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6. 15. A method of treating obstructive airway disease, comprising administering to a patient a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6.
RU2007126745/04A 2004-12-17 2005-12-14 Novel hydantoin derivatives as metalloproteinase inhibitors RU2378269C2 (en)

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